CN105073742B - Flap调节剂 - Google Patents

Flap调节剂 Download PDF

Info

Publication number
CN105073742B
CN105073742B CN201480019599.1A CN201480019599A CN105073742B CN 105073742 B CN105073742 B CN 105073742B CN 201480019599 A CN201480019599 A CN 201480019599A CN 105073742 B CN105073742 B CN 105073742B
Authority
CN
China
Prior art keywords
cyclobutyl
bases
amine
fluoro
pyrazine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201480019599.1A
Other languages
English (en)
Chinese (zh)
Other versions
CN105073742A (zh
Inventor
W.埃勒斯
A.E.皮茨格拉德
M.D.哈克
N.A.哈里鲁克
W.M.乔内斯
J.M.凯思
P.克罗祖克
A.D.勒布萨克
J.刘
N.S.马尼
K.J.麦克鲁雷
S.P.梅杜纳
M.D.罗森
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of CN105073742A publication Critical patent/CN105073742A/zh
Application granted granted Critical
Publication of CN105073742B publication Critical patent/CN105073742B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50Pyridazines; Hydrogenated pyridazines
    • A61K31/5025Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/06Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/73Unsubstituted amino or imino radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D237/00Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10Spiro-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10Spiro-condensed systems
    • C07D491/113Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/188Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Oncology (AREA)
  • Hospice & Palliative Care (AREA)
  • Vascular Medicine (AREA)
  • Psychiatry (AREA)
  • Dermatology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CN201480019599.1A 2013-02-04 2014-01-31 Flap调节剂 Expired - Fee Related CN105073742B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361760615P 2013-02-04 2013-02-04
US61/760615 2013-02-04
US201361798951P 2013-03-15 2013-03-15
US61/798951 2013-03-15
PCT/US2014/014088 WO2014121040A1 (en) 2013-02-04 2014-01-31 Flap modulators

Publications (2)

Publication Number Publication Date
CN105073742A CN105073742A (zh) 2015-11-18
CN105073742B true CN105073742B (zh) 2017-08-08

Family

ID=50102272

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201480019599.1A Expired - Fee Related CN105073742B (zh) 2013-02-04 2014-01-31 Flap调节剂

Country Status (14)

Country Link
US (4) US9073876B2 (ko)
EP (1) EP2951169B1 (ko)
JP (1) JP6328145B2 (ko)
KR (1) KR20160004258A (ko)
CN (1) CN105073742B (ko)
AU (2) AU2014212193B2 (ko)
BR (1) BR112015018504A2 (ko)
CA (1) CA2899904A1 (ko)
EA (1) EA030404B1 (ko)
HK (1) HK1217489A1 (ko)
MX (1) MX364069B (ko)
TW (1) TWI644899B (ko)
UY (1) UY35305A (ko)
WO (1) WO2014121040A1 (ko)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI644899B (zh) 2013-02-04 2018-12-21 健生藥品公司 Flap調節劑
US9745328B2 (en) 2013-02-04 2017-08-29 Janssen Pharmaceutica Nv Flap modulators
US9718816B2 (en) 2013-03-15 2017-08-01 Epizyme, Inc. 1-phenoxy-3-(alkylamino)-propan-2-ol derivatives as CARM1 inhibitors and uses thereof
BR112015022787A2 (pt) 2013-03-15 2017-11-07 Epizyme Inc compostos, composições farmacêuticas, kit ou artigo farmacêutico embalado, e método de tratamento de um distúrbio mediado por carm1
US9346802B2 (en) 2013-03-15 2016-05-24 Epizyme, Inc. CARM1 inhibitors and uses thereof
WO2016044641A2 (en) * 2014-09-17 2016-03-24 Epizyme, Inc. Carm1 inhibitors and uses thereof
CN104961642A (zh) * 2015-06-26 2015-10-07 华中药业股份有限公司 一种合成普萘洛尔的新方法
CN108026079B (zh) 2015-09-24 2020-09-22 株式会社Lg化学 化合物和包含其的有机发光器件
CN108329330B (zh) * 2017-01-20 2021-05-04 复旦大学 2-苄氧苯基噁唑并吡啶类化合物及其药物用途
KR20210116549A (ko) 2019-01-18 2021-09-27 아스트라제네카 아베 Pcsk9 억제제 및 이의 이용 방법
JP7486382B2 (ja) 2020-08-31 2024-05-17 東京エレクトロン株式会社 搬送装置および搬送方法
WO2022166920A1 (zh) * 2021-02-08 2022-08-11 杭州中美华东制药有限公司 一种吡咯并哒嗪类化合物及其制备方法和用途

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1052306A (zh) * 1988-12-07 1991-06-19 惠尔康基金会集团公司 对中枢神经系统具有药理活性的化合物
CN101356169A (zh) * 2005-11-04 2009-01-28 辉瑞有限公司 吡嗪衍生物
EP2471776A1 (de) * 2010-12-28 2012-07-04 Bayer CropScience AG Pyridin-2-ylpropandinitrile und deren Verwendung als Herbizide
WO2012121939A2 (en) * 2011-03-04 2012-09-13 Locus Pharmaceuticals, Inc. Aminopyrazine compounds

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5550138A (en) 1992-03-25 1996-08-27 Takeda Chemical Industries, Ltd. Condensed thiadiazole derivative, method of its production, and use thereof
AT400845B (de) 1993-12-06 1996-03-25 Chem Pharm Forsch Gmbh Neue thienothiazinderivate, ein verfahren zu ihrer herstellung und ihre verwendung
US5780473A (en) 1995-02-06 1998-07-14 Bristol-Myers Squibb Company Substituted biphenyl sulfonamide endothelin antagonists
FR2766822B1 (fr) 1997-07-30 2001-02-23 Adir Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JP2002536446A (ja) 1999-02-09 2002-10-29 3−ディメンショナル ファーマシューティカルズ, インコーポレイテッド プロテアーゼ阻害剤としての、ヘテロアリールアミジン類、メチルアミジン類およびグアニジン類
WO2001074793A2 (en) 2000-04-03 2001-10-11 3-Dimensional Pharmaceuticals, Inc. Substituted thiazoles and the use thereof as inhibitors of plasminogen activator inhibitor-1
US20020198219A1 (en) 2000-08-08 2002-12-26 Grant Elfrida R. 2-pyridinamine compositions and related methods
IL153995A0 (en) 2000-08-11 2003-07-31 Eisai Co Ltd 2-aminopyridine derivatives and pharmaceutical compositions containing the same
WO2002022605A1 (en) 2000-09-15 2002-03-21 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
WO2002057216A1 (fr) 2001-01-18 2002-07-25 Shionogi & Co., Ltd. Composes de terphenyle supportant des groupes amino substitues
EP1354877A1 (en) 2001-01-22 2003-10-22 Shionogi & Co., Ltd. Hetero-tricyclic compounds having substituted amino groups
EP1389616B1 (en) 2001-04-27 2011-07-27 Mitsubishi Tanabe Pharma Corporation 3,4-Dihalobenzylpiperidine derivatives and their medical use
WO2003007955A2 (en) 2001-07-20 2003-01-30 Cancer Research Technology Limited Biphenyl apurinic/apyrimidinic site endonuclease inhibitors to treat cancer
FR2831536A1 (fr) 2001-10-26 2003-05-02 Aventis Pharma Sa Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr
WO2003082869A1 (en) 2002-03-28 2003-10-09 Eisai Co., Ltd. Azaindoles as inhibitors of c-jun n-terminal kinases
GB0209891D0 (en) 2002-04-30 2002-06-05 Glaxo Group Ltd Novel compounds
AU2003251970A1 (en) 2002-07-18 2004-02-09 Bristol-Myers Squibb Company Modulators of the glucocorticoid receptor and method
GB0400895D0 (en) 2004-01-15 2004-02-18 Smithkline Beecham Corp Chemical compounds
DE102004008141A1 (de) 2004-02-19 2005-09-01 Abbott Gmbh & Co. Kg Guanidinverbindungen und ihre Verwendung als Bindungspartner für 5-HT5-Rezeptoren
AU2005236055B2 (en) 2004-04-20 2011-10-06 Transtech Pharma, Llc Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators
US20050245543A1 (en) 2004-04-30 2005-11-03 Pfizer Inc Histamine-3 receptor antagonists
DE102004028862A1 (de) 2004-06-15 2005-12-29 Merck Patent Gmbh 3-Aminoindazole
AR050917A1 (es) 2004-08-13 2006-12-06 Amphora Discovery Corp Compuestos basados en 2-amido-tiazol que presentan actividad inhibidora de enzimas que utilizan atp, y composiciones y usos de los mismos
US20100286211A1 (en) 2004-10-08 2010-11-11 Biswajit Das Oxazolidinone derivatives as antimicrobials
EP1828180A4 (en) 2004-12-08 2010-09-15 Glaxosmithkline Llc 1H-pyrrolo [2,3-BETA] PYRIDINE
WO2006074262A1 (en) 2005-01-05 2006-07-13 Rigel Pharmaceuticals, Inc. Ubiquitin ligase inhibitors
TW201431849A (zh) 2005-06-06 2014-08-16 Lilly Co Eli Ampa受體強化劑
WO2007034282A2 (en) 2005-09-19 2007-03-29 Pfizer Products Inc. Diaryl-imidazole compounds condensed with a heterocycle as c3a receptor antagonists
US7405302B2 (en) 2005-10-11 2008-07-29 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (FLAP) inhibitors
CA2626103C (en) * 2006-01-13 2013-07-30 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
CN102977036B (zh) 2006-01-13 2017-05-03 美国陶氏益农公司 2‑(多取代芳基)‑6‑氨基‑5‑卤代‑4‑嘧啶甲酸及其作为除草剂的用途
KR101456721B1 (ko) 2006-03-31 2014-10-31 노파르티스 아게 신규 화합물
KR100969686B1 (ko) 2006-08-07 2010-07-14 한국과학기술연구원 신규한 티아졸계 화합물 및 이를 함유하는 t-형 칼슘 채널저해제
FR2906250B1 (fr) 2006-09-22 2008-10-31 Sanofi Aventis Sa Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique
JP2009023986A (ja) * 2006-11-08 2009-02-05 Pharma Ip 抗癌剤としてのビアリール誘導体
EP1964840A1 (en) 2007-02-28 2008-09-03 sanofi-aventis Imidazo[1,2-a]pyridines and their use as pharmaceuticals
WO2008150899A1 (en) 2007-05-29 2008-12-11 Emory University Combination therapies for treatment of cancer and inflammatory diseases
US8207179B2 (en) 2007-06-12 2012-06-26 Boehringer Ingelheim International Gmbh Substituted indolines as tyrosine kinase inhibitors
AU2009212135B2 (en) 2008-02-07 2014-08-21 Massachusetts Eye & Ear Infirmary Compounds that enhance Atoh-1 expression
EP2107054A1 (en) 2008-04-01 2009-10-07 Università Degli Studi Di Milano - Bicocca Antiproliferative compounds and therapeutic uses thereof
CA2720654A1 (en) 2008-04-22 2009-10-29 Merck Frosst Canada Ltd. Novel substituted heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase
US9315449B2 (en) 2008-05-15 2016-04-19 Duke University Substituted pyrazoles as heat shock transcription factor activators
US8853420B2 (en) 2008-07-29 2014-10-07 Boehringer Ingelheim International Gmbh Compounds
WO2010019828A1 (en) 2008-08-13 2010-02-18 Metabasis Therapeutics, Inc. Glucagon receptor antagonists
US8586754B2 (en) * 2008-12-05 2013-11-19 Abbvie Inc. BCL-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases
NZ595819A (en) 2009-04-02 2013-02-22 Merck Serono Sa DIHYDROOROTATE DEHYDROGENASE INHIBITORS; benzimidazole-4-carboxylic acid
EP2443096A1 (en) 2009-06-19 2012-04-25 AstraZeneca AB Pyrazine carboxamides as inhibitors of dgat1
WO2011047129A1 (en) 2009-10-15 2011-04-21 Southern Research Institute Treatment of neurodegenerative diseases, causation of memory enhancement, and assay for screening compounds for such
US20110269759A1 (en) 2009-10-30 2011-11-03 Coats Steven J Pyrimidine compounds as delta opioid receptor modulators
US8420655B2 (en) * 2009-12-04 2013-04-16 Boehringer Ingelheim International Gmbh Benzimidazole inhibitors of leukotriene production
CA2781888C (en) 2009-12-11 2019-06-18 Nono Inc. Agents and methods for treating ischemic and other diseases
CA2786314A1 (en) 2010-02-25 2011-09-01 Merck Sharp & Dohme Corp. Novel cyclic benzimidazole derivatives useful anti-diabetic agents
AU2011276539A1 (en) 2010-06-28 2013-02-07 President And Fellows Of Harvard College Compounds for the inhibition of cellular proliferation
JP5928958B2 (ja) * 2010-10-29 2016-06-01 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ロイコトリエン生成のベンゾイミダゾールインヒビター
PE20140859A1 (es) 2011-02-25 2014-07-25 Merck Sharp & Dohme Novedosos derivados de azabencimidazol ciclico utiles como agentes antidiabeticos
WO2012119978A1 (en) 2011-03-07 2012-09-13 Glaxosmithkline Llc Quinolinone derivatives
WO2012166145A1 (en) 2011-06-02 2012-12-06 Lawrence Livermore National Security, Llc Charged particle focusing and deflection system utlizing deformed conducting electrodes
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
TWI644899B (zh) 2013-02-04 2018-12-21 健生藥品公司 Flap調節劑
US9745328B2 (en) 2013-02-04 2017-08-29 Janssen Pharmaceutica Nv Flap modulators

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1052306A (zh) * 1988-12-07 1991-06-19 惠尔康基金会集团公司 对中枢神经系统具有药理活性的化合物
CN101356169A (zh) * 2005-11-04 2009-01-28 辉瑞有限公司 吡嗪衍生物
EP2471776A1 (de) * 2010-12-28 2012-07-04 Bayer CropScience AG Pyridin-2-ylpropandinitrile und deren Verwendung als Herbizide
WO2012121939A2 (en) * 2011-03-04 2012-09-13 Locus Pharmaceuticals, Inc. Aminopyrazine compounds

Also Published As

Publication number Publication date
CN105073742A (zh) 2015-11-18
EA030404B1 (ru) 2018-07-31
MX2015010106A (es) 2016-01-14
AU2017213500A1 (en) 2017-08-31
US10047101B2 (en) 2018-08-14
US20150252008A1 (en) 2015-09-10
US9926333B2 (en) 2018-03-27
AU2014212193A1 (en) 2015-07-30
US9732093B2 (en) 2017-08-15
US9073876B2 (en) 2015-07-07
WO2014121040A8 (en) 2015-02-12
JP6328145B2 (ja) 2018-05-23
MX364069B (es) 2019-04-10
US20140221310A1 (en) 2014-08-07
JP2016514089A (ja) 2016-05-19
US20150368270A1 (en) 2015-12-24
EP2951169A1 (en) 2015-12-09
EP2951169B1 (en) 2019-08-28
AU2014212193B2 (en) 2017-06-15
KR20160004258A (ko) 2016-01-12
WO2014121040A1 (en) 2014-08-07
TWI644899B (zh) 2018-12-21
CA2899904A1 (en) 2014-08-07
AU2017213500B2 (en) 2019-02-28
US20170327514A1 (en) 2017-11-16
TW201444799A (zh) 2014-12-01
UY35305A (es) 2014-08-29
HK1217489A1 (zh) 2017-01-13
EA201591451A1 (ru) 2015-12-30
BR112015018504A2 (pt) 2017-07-18

Similar Documents

Publication Publication Date Title
CN105073742B (zh) Flap调节剂
CN103429585B (zh) 作为白细胞介素-1受体相关激酶抑制剂的吲唑基三唑衍生物
CN101029022B (zh) 含氮芳环衍生物的制备方法
JP6082409B2 (ja) 3−アリール−5−置換イソキノリン−1−オン化合物及びその治療的使用
TWI706939B (zh) 新穎二取代1,2,4-三化合物
CN101790526A (zh) 用作激酶抑制剂的5-杂芳基取代的吲唑化合物
WO2012149528A1 (en) Inhibitors of inducible form of 6-phosphofructose-2-kinase
US9884878B2 (en) FLAP modulators
CN105849098A (zh) Gsk-3抑制剂
WO2005023782A1 (ja) 置換された縮環ピリミジン-4(3h)-オン化合物
US10633350B2 (en) Diphenyl derivatives and uses thereof
EP3026043A1 (en) Glycine transporter inhibitor
KR20230027059A (ko) H-pgds를 저해하는 축환 화합물
CN101983010A (zh) 双药效团-pde4-毒蕈碱拮抗剂
WO2024121779A1 (en) Papain-like protease (plpro) inhibitors
TW202328076A (zh) Sos1抑制劑及其用途

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170808

Termination date: 20200131

CF01 Termination of patent right due to non-payment of annual fee